A Direct Reduction of Aliphatic Aldehyde, Acyl Chloride, Ester, and Carboxylic Functions into a Methyl Group

Vladimir Gevorgyan*, Michael Rubin, Jian-Xiu Liu and Yoshinori Yamamoto

*Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, Illinois 60607-7061, Email: vladuic.edu

V. Gevorgyan, M. Rubin, J.-X. Liu, Y. Yamamoto, J. Org. Chem, 2001, 66, 1672-1675.

DOI: 10.1021/jo001258a

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Abstract

Aliphatic carboxyl derivatives (acids, acyl chlorides, esters) and aldehydes were efficiently reduced to the methyl group by HSiEt₃ in the presence of catalytic amounts of B(C₆F₅)₃. Aromatic carboxylic acids, as well as other carbonyl functional equivalents, underwent smooth partial reduction to the corresponding TES-protected benzylic alcohols.

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Key Words

Deoxygenations, Alcohol Synthesis, Silyl Ethers, Triethylsilane

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ID: J42-Y2001-570